Special Issue "Catalyzed Mizoroki–Heck Reaction or C–H activation"

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Metal Catalysis".

Deadline for manuscript submissions: closed (31 March 2018)

Special Issue Editor

Guest Editor
Prof. Dr. Sabine Berteina-Raboin

University of Orléans, ICOA, Institute of Organic and Analytical Chemistry, UMR 7771, Rue de Chartres, BP 6759, F-45067 Orléans, France.
Website | E-Mail
Interests: Methodological studies in heterocyclic chemistry; formation of C-C, C-N, C-O and C-S bonds; Synthesis or hemi-synthesis of heterocyclic or bioactives molecules or natural products; environmentally friendly methods

Special Issue Information

Dear Colleagues,

In the last few decade, researches on the elaboration by palladium-catalytic processes of C-C bonds or the C–H bonds activation has grown considerably but many improvements are still possible in terms of selectivity or even enantioselectivity via the development of new ligands or the study of the catalytic effect of other metals to carry out the same chemical transformations.The attention paid to environmentally friendly methods in terms of the quantities of catalysts, ligands and solvents is currently indispensable. The Mizoroki-Heck reaction is one of these important catalytic method to generate C-C bonds in organic synthesis and is also possible by C-H activation. This Special Issue on « Catalyze Mizoroki-Heck Reaction or C-H activation » will focus on new advances in the formation of C-C bonds via the Mizoroki-heck reaction or new C-H activation methods. In doing so we placed specific emphasis on Original research papers and short reviews on synthesis of biologically active compounds using these catalytic processes, identification of new catalysts, synthesis of new ligands allowing selectivity or énantioselectivity of the synthetic processes, activity and stability of catalyst under turnover conditions and all improvements in catalytic processes for obtaining of C-C bond or the C-H bond activation.

Prof. Dr. Sabine Berteina-Raboin
Guest Editor

Manuscript Submission Information

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Keywords

  • Methodological studies in heterocyclic chemistry, formation of C-C, C-N, C-O and C-S bonds, Synthesis or hemi-synthesis of heterocyclic or bioactives molecules or natural products. environmentally friendly methods.

Published Papers (7 papers)

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Research

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Open AccessFeature PaperCommunication Palladium-Catalyzed Regioselective Alkoxylation via C-H Bond Activation in the Dihydrobenzo[c]acridine Series
Catalysts 2018, 8(4), 139; https://doi.org/10.3390/catal8040139
Received: 12 March 2018 / Revised: 26 March 2018 / Accepted: 29 March 2018 / Published: 31 March 2018
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Abstract
5,6-Dihydrobenzo[c]acridine belongs to the large aza-polycyclic compound family. Such molecules are not fully planar due to the presence of a partially hydrogenated ring. This paper describes the first Pd-catalyzed alkoxylation via C-H bond activation of variously substituted 5,6-dihydrobenzo[c]acridines. We
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5,6-Dihydrobenzo[c]acridine belongs to the large aza-polycyclic compound family. Such molecules are not fully planar due to the presence of a partially hydrogenated ring. This paper describes the first Pd-catalyzed alkoxylation via C-H bond activation of variously substituted 5,6-dihydrobenzo[c]acridines. We determined suitable conditions to promote the selective formation of C-O bonds using 10% Pd(OAc)2, PhI(OAc)2 (2 eq.) and MeOH as the best combination of oxidant and solvent, respectively. Under these conditions, 5,6-dihydrobenzo[c]acridines bearing substituents at both rings A and D were successfully functionalized, giving access to polysubstitutited acridine motifs. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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Open AccessFeature PaperArticle The First Catalytic Direct C–H Arylation on C2 and C3 of Thiophene Ring Applied to Thieno-Pyridines, -Pyrimidines and -Pyrazines
Catalysts 2018, 8(4), 137; https://doi.org/10.3390/catal8040137
Received: 13 March 2018 / Revised: 27 March 2018 / Accepted: 28 March 2018 / Published: 30 March 2018
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Abstract
A practical one-pot procedure for the preparation of diverse thieno[3,2-d]pyrimidines is reported here for the first time. This two-step process via C–H activation in position C-2 of thiophene led to the development of an improved methodology for the synthesis of numerous
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A practical one-pot procedure for the preparation of diverse thieno[3,2-d]pyrimidines is reported here for the first time. This two-step process via C–H activation in position C-2 of thiophene led to the development of an improved methodology for the synthesis of numerous compounds. This new methodology is an efficient alternative to the conventional methods currently applied. The C–H activation of the thiophene C-3 position was also achieved and can be selective. The optimized conditions can also be applied to thienopyridines and thienopyrazines. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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Open AccessArticle MgAl-Layered Double Hydroxide Solid Base Catalysts for Henry Reaction: A Green Protocol
Catalysts 2018, 8(4), 133; https://doi.org/10.3390/catal8040133
Received: 28 February 2018 / Revised: 24 March 2018 / Accepted: 27 March 2018 / Published: 29 March 2018
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Abstract
A series of MgAl-layered double hydroxide (MgAl-HT), the calcined form at 500 °C (MgAlOx), and the rehydrated one at 25 °C (MgAl-HT-RH) were synthesized. Physicochemical properties of the catalysts were characterized by X-ray diffraction (XRD) and scanning electron microscopy (SEM). Surface
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A series of MgAl-layered double hydroxide (MgAl-HT), the calcined form at 500 °C (MgAlOx), and the rehydrated one at 25 °C (MgAl-HT-RH) were synthesized. Physicochemical properties of the catalysts were characterized by X-ray diffraction (XRD) and scanning electron microscopy (SEM). Surface area of the as-synthesized, calcined, and rehydrated catalysts was determined by N2 physisorption at −196 °C. CO2 temperature-programmed desorption (CO2-TPD) was applied to determine the basic sites of catalysts. The catalytic test reaction was carried out using benzaldehyde and their derivatives with nitromethane and their derivatives. The Henry products (1–15) were obtained in a very good yield using MgAl-HT-RH catalyst either by conventional method at 90 °C in liquid phase or under microwave irradiation method. The mesoporous structure and basic nature of the rehydrated solid catalyst were responsible for its superior catalytic efficiency. The robust nature was determined by using the same catalyst five times, where the product % yield was almost unchanged significantly. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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Open AccessFeature PaperArticle Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives
Catalysts 2018, 8(3), 115; https://doi.org/10.3390/catal8030115
Received: 28 February 2018 / Revised: 12 March 2018 / Accepted: 13 March 2018 / Published: 15 March 2018
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Abstract
Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a
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Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a pallado-catalyzed Mizoroki-Heck cross-coupling as key reaction performed in solvent and ligand free conditions. After a careful optimization, we succeeded in accessing various (E/Z)-dienes and (E/E/Z)-trienes in moderate to good yields without isomerization and applied the same approach to the synthesis of ABA in an environmentally sound manner. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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Review

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Open AccessReview Advances in Enantioselective C–H Activation/Mizoroki-Heck Reaction and Suzuki Reaction
Catalysts 2018, 8(2), 90; https://doi.org/10.3390/catal8020090
Received: 31 January 2018 / Revised: 14 February 2018 / Accepted: 15 February 2018 / Published: 23 February 2018
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Abstract
Traditional cross-coupling reactions, like Mizoroki-Heck Reaction and Suzuki Reaction, have revolutionized organic chemistry and are widely applied in modern organic synthesis. With the rapid development of C–H activation and asymmetric catalysis in recent years, enantioselective C–H activation/cross-coupling reactions have drawn much attention from
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Traditional cross-coupling reactions, like Mizoroki-Heck Reaction and Suzuki Reaction, have revolutionized organic chemistry and are widely applied in modern organic synthesis. With the rapid development of C–H activation and asymmetric catalysis in recent years, enantioselective C–H activation/cross-coupling reactions have drawn much attention from researchers. This review summarizes recent advances in enantioselective C–H activation/Mizoroki-Heck Reaction and Suzuki Reaction, with emphasis on the structures and functions of chiral ligands utilized in different reactions. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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Open AccessReview Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners
Catalysts 2018, 8(1), 23; https://doi.org/10.3390/catal8010023
Received: 27 December 2017 / Revised: 10 January 2018 / Accepted: 10 January 2018 / Published: 14 January 2018
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Abstract
The Mizoroki-Heck reaction represents one of the most convenient methods for carbon-carbon double bond formation in the synthesis of small organic molecules, natural products, pharmaceuticals, agrochemicals, and functional materials. Fluorine-containing organic compounds have found wide applications in the research areas of materials and
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The Mizoroki-Heck reaction represents one of the most convenient methods for carbon-carbon double bond formation in the synthesis of small organic molecules, natural products, pharmaceuticals, agrochemicals, and functional materials. Fluorine-containing organic compounds have found wide applications in the research areas of materials and life sciences over the past several decades. The incorporation of fluorine-containing segments into the target molecules by the Mizoroki-Heck reactions is highly attractive, as these reactions efficiently construct carbon-carbon double bonds bearing fluorinated functional groups by simple procedures. This review summarizes the palladium-catalyzed Mizoroki-Heck reactions using various fluorine-containing reagents as the cross-coupling partners. The first part of the review describes the Pd-catalyzed Mizoroki-Heck reactions of aryl halides or pseudo-halides with the fluorinated alkenes, and the second part discusses the Pd-catalyzed Mizoroki-Heck reactions of the fluorinated halides or pseudo-halides with alkenes. Variants of the Pd-catalyzed Mizoroki-Heck reactions with fluorine-containing reagents are also briefly depicted. This work supplies an overview, as well as a guide, to both younger and more established researchers in order to attract more attention and contributions in the realm of Mizoroki-Heck reactions with fluorine-containing participants. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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Open AccessReview Heck Reaction—State of the Art
Catalysts 2017, 7(9), 267; https://doi.org/10.3390/catal7090267
Received: 20 August 2017 / Revised: 5 September 2017 / Accepted: 6 September 2017 / Published: 11 September 2017
Cited by 4 | PDF Full-text (10451 KB) | HTML Full-text | XML Full-text
Abstract
The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing
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The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review. Full article
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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